Starting with cholic acid, the syntheses of simaroubaceous delta- lactone analogs of holacantone and quassin having potential antineoplastic properties are outlined. A unique D-ring cleavage is suggested and the synthesis of the heretofore first 8 Beta-methyl and 8 Beta-hydroxymethyl steroids precursors is outlined. Application of D-ring cleavage on the 8 Beta-methyl steroids generates the first totally synthesized analogs holacanthone (glaucarubolone) and quassin.